


The Best Worst First Date

by sisforsterek



Series: The Crazy and Awesome Life We Live [2]
Category: Teen Wolf (TV)
Genre: Blow Jobs, Established Relationship, First Date, First Time Blow Jobs, M/M
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2018-12-03
Packaged: 2019-09-06 15:19:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,677
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16835254
Author URL: https://archiveofourown.org/users/sisforsterek/pseuds/sisforsterek
Summary: The first date where almost everything that can go wrong does, but it all works out in the end.





	The Best Worst First Date

**Author's Note:**

> You really should read the first part to understand certain things in this. 
> 
> Thanks to [misfitmonarchy](/users/misfitmonarchy/) for brainstorming a bit of this with me ages ago. Thanks to [thisnewjoe](/users/thisnewjoe/) for the beta!

Derek thought he was doing great when he was out the door and in his car fifteen minutes before he had planned to leave to pick up Stiles for their first official date. What he didn’t expect was for a wreck on the highway to hold up traffic. He’s already been stuck for twenty minutes waiting to be let through, and this area has horrible cell reception, so he can’t even let Stiles know that he’ll be late to pick him up.

They had been spending quite a bit of time together at the Stilinski house watching Netflix and cuddling on the couch while Stiles still had casts on his legs, but a couple weeks ago Stiles was finally able to get them removed. After two weeks of physical therapy, Stiles convinced Derek that he was ready to leave the house for something other than school or physical therapy, so Derek asked him out on what would be their first date that would take place outside of his house. Stiles will still have to use forearm crutches, but Derek assured him that it wouldn’t be an issue with the activities he had planned. Besides, if Stiles got tired, Derek would have no qualms carrying him.

Ten minutes after Derek was supposed to pick up Stiles, and just before he was ready to pull onto the side of the road and run the rest of the way to Stiles’ house, the cars in front of Derek finally moved. 

~’~’~

Fifteen minutes after Derek was supposed to pick him up, Stiles answers the door to find his boyfriend looking a little anxious.

“Sorry I’m late,” Derek quickly says. 

“I was beginning to think you’d changed your mind,” Stiles replies, leaning on his crutches.

“I was stuck in traffic for twenty-five minutes due to a wreck, and there was no cell reception. I’m sorry I made you think that, but you have to know I wouldn’t stand you up,” Derek tells him.

“Relax, let’s just get this show on the road. What do you have planned? You’ve been so secretive about this date. I love a good mystery, but I realized when I was getting dressed that I didn’t know how I should dress, and you weren’t answering my calls, so I hope this is okay?” Stiles says, gesturing to himself.

Derek glances at his boyfriend, letting his eyes rake up his body, starting at his Chuck Taylors, and then up to his black jeans and royal blue dress shirt with the sleeves rolled up to mid-forearms and the top two buttons undone. His hair is even styled in a way that makes his hair look soft, yet perfectly in place. Derek is impressed.

“You clean up nicely,” Derek says with a smirk.

Stiles just rolls his eyes.

“I’m glad to see you’ve reclaimed the bad boy look,” Stiles replies, gesturing at Derek’s black leather jacket.

“You said you liked it, so…” Derek trails off.

“Oh, I do,” Stiles tells him, wiggling his eyebrows as he steps forward, legs shaky from standing in one place for more than a minute. 

Derek catches him easily as Stiles gives him a quick peck on his lips before taking a step back. 

~’~’~

“Did anyone call to give you the good news yet? Dad just told me before you picked me up. I don’t know why they waited so long. I don’t even think they were going to do anything if I hadn’t sent an emotional letter to her office. It’s just like government, though. They never want to admit that us little people can get stuff done. It’s-“ Stiles rants.

“What are you talking about?” Derek interrupts, because he knows if he doesn’t, Stiles will talk all the way to the restaurant, and by then, not even Derek will remember what the original point was. 

He loves the guy, but sometimes he has to steer the conversation if they ever want to actually have one.

“The Good Samaritan Medal?” Stiles asks.

“I don’t know what you’re talking about,” Derek answers.

“I knew no one told you! You’re going to get an award from the city of Beacon Hills, from the Mayor’s office, because you found me and the other victims. It’ll make for a great headline.” Stiles spreads his hands out in front of himself as he says, “Former murder suspect finds hostages on his morning jog.” He drops his hands and turns to Derek with a smirk. “Scott doesn’t get an award, since the official story has him being abducted after he left school _sick_. Serves him right, since most of the murder suspect thing was his fault anyway.” Stiles finishes with a pat to Derek’s thigh.

Suddenly the car swerves and a rhythmic loud noise like something beating against the car starts up.

“Shit. No, no, no,” Derek says as he steers the camaro to the side of the road.

“It’s just a flat tire,” Stiles says as Derek opens the door.

“We were already running late for our reservation. Stay here, I’ve got a spare in the trunk,” Derek says.

“Or you could just run back and get my Jeep. It’ll be quicker than changing a tire, with how fast you can run,” Stiles suggests. 

Derek pauses before slamming his door. “Stiles, I’m not leaving you alone in a black car on the side of the road when it’s dark. I’ll just change the tire and we’ll see if the restaurant can work us in when we get there.”

Stiles rolls down his window to continue the conversation, “That’s what emergency flashers are for, by the way. They exist to make dark cars visible at night.”

“I’m not leaving you alone on the side of the road at night,” Derek says before he opens the camaro’s trunk.

“Derek Hale. Who knew he’d be such a gentleman?” Stiles smiles to himself.

~’~’~

“They said the wait is an hour,” Derek exhales roughly as he slides back into the driver’s seat.

“We can just eat somewhere else. I’ll be happy with a cheeseburger, curly fries, and a chocolate shake from my favorite diner. You don’t have to take me to a steakhouse to please me,” Stiles says with a grin.

“You’re sure?” Derek asks, turning to Stiles. 

His whole posture screams stressed out, and Stiles’ grin only gets bigger. Derek Hale wanted to wine and dine him—without the wine, because Stiles _is_ only eighteen—at the most expensive place in Beacon Hills.

“It doesn’t matter where we eat, as long as I’m with you,” Stiles replies, and Derek can hear by his heartbeat that he means it.

~’~’~

“I know you don’t even like zombies, but if you really want to see this movie with me, I can always order tickets online and we can go see it tomorrow,” Stiles says as Derek helps him get back in the car.

Derek nods, but Stiles can tell he’s disappointed that yet another activity tonight hasn’t gone according to plan. They had decided to just eat at the movie theater after they missed their dining reservation, since their menu offered all of Stiles’ favorites. It’s not Derek’s fault that the bowling alley caught fire overnight or that the ice skating rink lost power when a car hit the utility pole on its corner, and because of those things everyone in town decided to see a movie on a Friday night, and by the time Stiles and Derek made it to the theater, everything was sold out except some musical—and the previews for it sparked zero interest in either of them.

“I just know you really want to see Pride and Prejudice and Zombies,” Derek says.

“And it doesn’t matter if I see it tomorrow. What I really wanted to do tonight was spend time with you outside my house,” Stiles says before leaning forward and pecking Derek on the cheek.

A small smile graces Derek’s face before he says, “Okay,” and then closes Stiles’ door.

“But I think it’s really cute you tried to pay those girls double to buy their tickets. Alright, let’s just head to the diner and eat, because now I’m starving. Then we can just head back to your place,” Stiles says when Derek slides into the driver’s seat beside him.

Derek turns to look at Stiles. “I thought the whole point of tonight was that you wanted to get out of your house.”

“And I didn’t suggest spending time at my house. I said your place, Silly Wolf,” Stiles replies.

Derek momentarily debates telling Stiles not to call him that, but he secretly likes Stiles’ nicknames for him, so he just says “Okay.” and starts the car. 

~’~’~

When they walk into the diner, Stiles immediately sees the rest of the pack—minus Peter—in the big corner booth. Scott sees them first and waves them over. 

“Let’s go sit with them,” Stiles says and starts slowly walking that way, his forearm crutches clacking against the tile floor.

Derek follows behind, his lips pressed firmly together as he sighs. A group date was not what he had in mind for tonight, either, but this is his pack, and he can think of worse things to go wrong on this date night than a group date.

Derek pulls a chair up for Stiles to sit on, so he doesn’t have to try sliding into the booth, and then slides in the booth to Stiles’ left. He nods at the group, his pack, and listens as they pick up the conversation from before they walked into the diner.

“Welcome to Charlie’s. I’m Hunter, and I’ll be serving you today. The special is honey teriyaki glazed salmon with steamed veggies and a baked potato. What can I get you to drink?” Their waiter asks as he approaches their table.

“Dr. Pepper,” Stiles answers, while Derek orders a water.

“I’ll get those for you and give you a few minutes to look over the menu,” Hunter says and Derek tenses when Hunter’s hand grazes his shoulder.

While werewolves are tactile creatures, they don’t like to be touched by strangers. It’s all about the scent of pack, and Hunter is not pack.

Stiles doesn’t notice, as he’s already busy telling Lydia about their date night so far.

When Hunter returns with their drinks, he takes Stiles’ order first. Then he turns to Derek and says, “And what can I get for you, handsome?” Stiles snorts and Derek debates kicking him under the table, only stopping when he remembers that Stiles has recently had two broken legs.

~’~’~

Derek was a sensitive kid, always happy to hear stories of how his parents met, their meet-cute, as Laura had called it. He always looked forward to meeting his future wife, because his parents had been the perfect example of a couple in love. At the time he had only been attracted to girls. It wasn’t until Stiles explained the definition of pansexual to Derek that he’d finally understood his own sexuality. 

While Talia was quick to point out that werewolves didn’t have mates — at least not true mates that were meant for each other — Derek would still realize the potential of his future partner once he got to know them. First Derek had thought it was Paige, but now he realizes that while he found her very attractive, it was just the chase that excited him, as she’d played hard to get. With Kate, it was the idea of sneaking around, but he now realizes that should have been a red flag. With Stiles, he truly understands that he didn’t feel near what he felt for Paige or Kate, or any other girl he dated before, as he feels for Stiles. He can see all of the good qualities in Stiles that makes him perfect for Derek. If only their waiter would take the hint and stop flirting with him.

Stiles notices Derek’s discomfort because of Hunter’s interactions with Derek and says, “Why don’t you just tell him you’re taken?”

“I shouldn’t have to. Besides, I don’t want to make a thing out of it,” Derek replies.

When Hunter brings the bill, he sets one in front of Stiles and hands one to Derek, with his number on it. Derek snatches Stiles’ bill and sets it on top of his own.

“Hey! I can pay for my own meal,” Stiles says.

“This is supposed to be a date, and I asked you, so I’m buying,” Derek tells him.

“Thanks, babe, but this doesn’t mean I’m putting out,” Stiles says before cracking up at his own joke.

Derek rolls his eyes but leans over to kiss Stiles’ cheek anyway.

“I’d put out,” Derek hears Hunter mumble as he walks away from the table.

Derek takes a deep breath and closes his eyes to avoid accidentally flashing them in public. He can feel his claws sliding out and quickly puts his hands under the table.

“What’s wrong? I was joking,” Stiles says, face falling.

“It’s not you. The waiter just said he’d put out,” Derek tells him.

Stiles busts out laughing. “I guess I have competition then.”

“Hardly,” Derek says as Stiles presses a kiss to his cheek.

“Awww,” Lydia says.

Derek looks up and the rest of the pack are staring at them with smiles on their faces. It’s then that Derek realizes that even though tonight has not went as planned, spending time with the rest of the pack is still a good thing.

~’~’~

“Dad signed up for the overnight shift tonight. He said he figured I’d want to stay at your place, anyway. Believe me, that conversation was embarrassing for us both,” Stiles whispers into Derek’s ear as the werewolf carries him up the stairs to his loft as the elevator is, once again, broken. “We’ve enacted a ‘don’t ask, don’t tell’ policy, with the exception that I tell him if I’m staying overnight at your place, and never on a school night, even though there’s only two weeks left until—” Stiles stops talking once Derek has walked through the threshold of his bedroom door.

“I had my bedroom sound-proofed,” Derek says as he puts Stiles gently on his bed. 

Stiles doesn’t comment on the fact that Derek Hale—big strong werewolf that he is—is blushing, but he does say, “Well, this is presumptuous of you to take me straight to your bed.”

Derek ducks his head and misses Stiles’ grin as he starts to pull away and mumbles, “I just thought the bed would be more comfortable for you to watch a movie. You haven’t been able to prop your legs up all night. I thought—“ Stiles cuts Derek off with a kiss.

“You really are a sweetie,” Stiles says, his grin coming back. “Screw the movie.” 

Stiles pulls Derek on top of him and kisses him again as he wonders how he got so lucky.

“Are you in any pain?” Derek asks as he slides between Stiles’ legs.

“My thighs are a little sore, but it’s not too bad,” Stiles replies before kissing Derek again.

Stiles’ hands move down Derek’s back, finally settling on his amazing ass, while Derek slides his hands under Stiles’ shirt, resting them just above Stiles’ hips.

“That tickles,” Stiles says as he pulls back. “Oh, you’re taking my pain. You didn’t have to do that.”

“I want to,” Derek replies.

“That’s why I love you,” Stiles says and kisses Derek again.

“I still don’t know why I love you,” Derek snarks back.

Stiles leans forward and bites Derek on his neck as punishment.

Derek huffs out a laugh and bites Stiles’ neck right back, with his human teeth, of course. Stiles squirms and brushes his crotch against Derek’s in the process. 

“Oh God.” slips out of Stiles’ mouth. 

Derek replies, without missing a beat, “My name’s Derek.”

Stiles busts out laughing. “You’re such an ass.”

“Pot calling the kettle…” Derek says before kissing Stiles’ neck. His hand travels down Stiles’ side towards his zipper. 

“Point. Ooh, now we’re getting to the sexy time,” Stiles says as Derek slides down his zipper. 

“Dork,” Derek says as he tugs Stiles’ pants down. 

“Did you just call me a whale’s penis?” Stiles asks, mock horrified. 

“Well, you can be a dick at times,” Derek says, one eyebrow creeping toward his hairline. 

“Talk about the pot calling the kettle,” Stiles says as Derek moves off of Stiles to pull his pants the rest of the way off. 

Stiles looks to the side, suddenly embarrassed. 

“What’s wrong?” Derek asks. 

“My thighs look weird ever since I got the casts off,” Stiles answers. 

“It’s because you lost muscle mass while you couldn’t walk. You’ll get it back now that you’re in physical therapy. Besides, I don’t care about your thighs, though I am partial to your face and everything on the inside.” Derek playfully flashes his red eyes. 

Stiles smiles, “You’re such a sap.”

Derek just smiles and kisses him before tugging Stiles’ briefs down. He wraps a hand around Stiles’ cock and starts to stroke it.

“Nngg oh my god,” Stiles says as he bucks his hips toward Derek. “Oh, remind me not to do that. My thighs are still sore.”

“Want me to hold you down?” Derek asks.

“Oh God yes,” Stiles replies, “but first, I think you should get naked too. It’s only fair.”

Derek chuckles and gets off the bed. He quickly removes all of his clothes while Stiles watches with a hungry look in his eyes. 

“I can’t believe I finally get to see it,” Stiles says. 

“Finally?”

“Well I have been imagining what it looks like since I was sixteen.”

“I hope it lives up to your expectations.”

“Does it ever! I just want to put my mouth on it,” Stiles tells him as he sits up and scoots to the edge of the bed. 

“I’m not going to stop you,” Derek says as he steps closer to the bed.

Stiles reaches out and grabs Derek’s cock with one hand. It’s even larger than he expected, but not quite as thick. It’s uncut, and Stiles thinks it’s beautiful. His mouth waters as he leans forward and licks the tip. The flavor isn’t unpleasant, just different, so he quickly takes the tip in his mouth, using his tongue to work in between the foreskin.

Stiles has been reading all of the sex blogs for blowjob tips, so he knows to just use his hands on what won’t fit in his mouth. He reaches back with his other hand and starts massaging Derek’s balls, which earns a choked moan from his boyfriend.

It doesn’t take long before Stiles’ jaw is aching, and he’s getting frustrated that Derek hasn’t come yet, so he pulls off and asks, “Am I bad at this or something?”

“What? No!” Derek assures him.

“Okay, I just wondered why you haven’t come yet,” Stiles says as he rubs his jaw.

“Werewolf stamina. Trust me, your mouth feels amazing, but it’s okay if your jaw is sore. Your hand feels amazing too.”

Stiles grins and leans forward, taking just the tip in his mouth and jacking off the rest at a fast speed. He sucks hard and Derek stumbles forward a bit before he comes with no warning to Stiles. Stiles tries to swallow it all, but it’s a lot and some dribbles out of the corner of his mouth. He pulls off and takes a few deep breaths. Derek wipes at the corner of Stiles’ mouth and pushes it back in with his thumb. Then Stiles is sucking on Derek’s thumb, and Derek is left wondering how quickly he can get hard again.

“You’re amazing,” Derek says as he pushes Stiles backwards on the bed and kisses him, getting a taste of himself. He enjoys just kissing his boyfriend for a few moments, but then remembers that Stiles hasn’t come yet, so he kneels on the floor between his legs.

“Oh God,” Stiles says.

Derek chuckles. He’s never sucked a dick before, but Stiles didn’t seem to have much trouble, so he figures it can’t be too hard. He doesn’t waste any time and leans in to take as much of Stiles as he can fit in his mouth. Stiles is fairly big, and he only makes it about halfway before he starts to gag and has to pull back. He wraps a hand around the rest and gives him a slight squeeze before pulling back and sliding down again. 

“Holy shit,” Stiles says and Derek chuckles.

The taste is much better than he expected. He just tastes like Stiles, only stronger.

Stiles hands are in his hair before he knows it and he’s tugging slightly. It feels good and Derek moans in appreciation.

“Ohmygod, do that again,” Stiles cries, so Derek hums and Stiles moans. 

Derek remembers that Stiles had massaged his balls, so he reaches between his legs and does the same for him.

“This is going to be over embarrassingly fast,” Stiles says as he squirms a bit on the bed.

Derek pulls back and says, “I won’t judge.” Then he takes Stiles in his mouth again and it’s pretty much just repetitive motions to get him off from there. At the last minute he thinks to slide a finger around his hole and Stiles squeaks in a very unmanly fashion before shooting down his throat. Derek licks him dry and then joins Stiles in the bed.

Stiles turns his head to grin at Derek. He lets Derek move him until they’re fully on the bed and pressed together. Then he pulls him close for a lazy kiss.

“That was the best orgasm I’ve ever had, hands down,” Stiles tells him.

“I’m glad,” Derek replies.

Stiles looks at him for a moment before saying, “You really are, aren’t you?”

Derek grins and nods in answer.

“God, I love you,” Stiles says and kisses him again.

“I love you too,” Derek says when they come up for air. 

And he’s going to spend the rest of his life showing Stiles just how much he loves him.


End file.
